Derivatives of suprarenin and process of preparing the same



Patented Oct, 30, 1923,, V

UNITED {STATES PATENT OFFmEt CASIMIR FUNK LOUIS FREEDMAN, OF NEW YORK, N. Y., ASSIGNORS TO HERMAN A. METZ, OF NEW YORK, N. Y.

DERIVATIYES OF SUPRARENIN AND PROCESS OF PREPARING THE SAME.

No Drawing.

of derivatives of suprarenin represented by the general formula (OH) C H -CllnOR) --OH NHX in which R stands for an alkyl or aryl group and X stands for hydrogen or an alkyl' group, b the action of alcohols 1n the presence 0 mineral acids or other dehydrating agents or by the action of alkyl halides or other alkyl derivatives upon suprarenin base or salts thereof? The invention relates further to the prep jaration of new suprarenin compounds of higher molecular weight, said compounds 9 probably being a combination of two molecules of suprarenin in the nature of a lac tone;

The invention is illustratedby the following specific example.

1 part by weight of racemio suprarenin hydrochloride or its base is heated under reflux for several hours, say from 2. to 5 hours or longer, with 10 parts by weight of absolute ethyl alcohol containing in solution dry hydrochloric acid gas in quantity amounting to from 1 to 4 molecular equivalents of the suprarenin.

The reaction mixture is then cooled whereupon the new suprarenin derivative and the suprarenin compound of higher molecular weight crystallize in the form of their hydrochloride or hydrochloric acid compounds and are separated from mother liquor. The two products are then se arated from each other and purified by actional crystallization from absolute alcohol. The yield of the suprarenin derivative is about 40 per cent of the theoretical. The

Application filed August 4, 1822. Serial No. 579,744.

specific compound formed by the procedure described in the above example is the hydrochloride of 1.2 dihydroxy 4 methyl amino ethyl ethyLet-ol benzene, (methylamino ethyl ethanol pyrocatechol hydrochlpride) which is rep-resented by the formu a It crystallizes in the form of clusters of thin rectangular prisms, is readily soluble in hot absolute alcohol and in water and has a melting point of 169C. It is puri fied by recrystallization from hot absolute alcohol.

Other derivatives havin' the general formula (OH) C H -CH OR) CH NHX in which R stands for an aryl or alkyl group other than the ethyl cup and X stands for hydrogen or an alky group other than the methyl group may be prepared by substituting for the ortho-dioxyphenyl-ethanolmethylamin h drochlorid (racemic suprarenin hydrochlbrid) of the above exam 1e other starting materials in which the metl iyl group, represented by X in the above general formula is substituted by other groups and b substituting for the ethyl alcohol of the a ove example other alcohols or alkyl or aryl halides or derivatives.

The suprarenin compound of higher molecular weight formed as described in the above example amounts to about 10 per cent of the yield of the 'suprarenin derivative or about 4 per cent of the theoretical yield. The yield of this product varies with the amount of deh drating agent employed that is, hydrochlbric acid in the above ex ample, the maximum yield being obtained when about 4 molecular equivalents of hy drochloric acid are used. -The chemical constitution of the product is not definitely known although, as is stated above, it is thought to be a combination of two molecules of suprarenin in the form of a lactone. The hydrochloride crystallizes in the form of rectangular prisms having a melting point of 180 to 183 C. soluble in water but only sparingly soluble in hot 70 per cent alcohol. It is insoluble in hot absolute alcohol. Its solubility in alcohol in- "creases as the dilution of the alcohol increases.

We claim: 1. As new products, derivatives of orthodioxyphenylethanolaklylamin having the general formula,

(OH) ZOGH3CH(OR)CHZNHX in which R represents an alkyl group.

3. A derivative of ortho-dioxyphenylethanolmethylamin having the formula OH CH-GH OOH)- )2 8 3 2 5OHZNHOH3HCI,

said product forming by crystallization from alcoholic solution clusters of thin rectangular prismatic crystals having a melting point of 169 C.

4. Process of preparing methyl-aminoethyl ethanol pyrocatechol hydrochloride and a suprarenln compound of higher molecular weight which comprises heating for several hours a mixture of ortho-dioxyp11enylethanolmethylamin hydrochloride, ethyl alcohol, and hydrochloric acid. 7

5. Process of preparing derivatives of suprarenin which comprises reacting upon a suprarenin compound with an alkyl compound in the presence of a dehydrating agent.

6. Process of preparing derivatives of suprarenin and suprarenin compounds of higher molecular weight which comprises digesting a mixture containing suprarenin, an alcohol and a dehydrating agent. V

In testimony whereof, We afiix our signatures. Y

CASIMIR FUNK. LOUIS FREEDMAN; 

